Do what feels comfy for YOU Hammer - not what someone else feels you should do. I've never been one to dress trendy - I wear what I want when I want and don't give a flying fadoodle what anyone else thinks. If your sister-in-law doesn't like the way you dress - tell her that her moustache needs trimmed. (j/k of course)

i understand where your coming from hammer. i used to tuck my tshirt into my boxers then my outer shirt into my pants because you get less bunching going on. now i dont tuck anything in cause my belly doesnt allow it to often. but in all honesty do what is comfortable.

Well, I gotta chime in. I have to "dress for success" in my job, and it's sometimes important that I know exactly what is what. I hate to admit it, but I pay attention to things like the GQ Style Guy, and this is what he had to say on the matter in a recent column:

Q: Please settle a debate among friends. Two of my buddies tuck their undershirts into their underwear because they contend that when they don’t, their dress shirts easily become untucked. Besides the fact that it’s incredibly dorky and unstylish, I have never had a problem with shirts untucking. Even if I did, I would never stoop that low. What if they meet a nice lady, and things happen, and she gets down to the goods, and the guy’s undershirt is tucked into his drawers? That seems to be a surefire way to lose a girl’s interest.

A: I find in your favor, sir! Tucking the undershirt into the drawers is the quintessence of dorkiness. Some men do have a big recurring shirttail problem, and usually it is caused by (a) their trousers being too low in the rise or (b) their stomachs being too big for their britches. Some men obsess over this and go so far as to buy a paramilitary product known as shirt garters. Wearing shirt garters is beyond dorkiness—it’s totally highway-patrol anal.